1,4-Naphthoquinones in H-Bond-Directed Trienamine-Mediated Strategies

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• 作者：艁ukasz Albrecht ; Clarisa Villegas G贸mez ; Christian Borch Jacobsen ; Karl Anker J酶rgensen
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：June 21, 2013
• 年：2013
• 卷：15
• 期：12
• 页码：3010-3013
• 全文大小：258K
• 年卷期：v.15,no.12(June 21, 2013)
• ISSN：1523-7052

文摘

The synthesis of optically active, carboannulated dihydronaphthoquinone and naphthoquinone derivatives with up to four stereogenic centers is demonstrated by H-bond-directed, trienamine-mediated [4 + 2]-cycloadditions. The outcome of the reaction between 2,4-dienals and 1,4-naphthoquinones is controlled by the substituent in the 2-position of the 1,4-naphthoquinone. In the case of sterically demanding 2-substituted derivatives, dihydronaphthoquinones are obtained. However, when a hydrogen atom is present in the 2-position, a subsequent oxidation of the initially formed cycloadducts occurs yielding naphthoquinones.